68888-19-7

Upstream product

• 100-71-0 2-Ethylpyridine 
• 50-00-0 formaldehyd 
• 5029-67-4 2-iodopyridine 
• 107-18-6 allyl alcohol 
• 58379-60-5 2-(2-pyridinyl)-3-hydroxypropene 
• 109-04-6 2-bromo-pyridine 
• 67-56-1 methanol 
• 103-74-2 2-(2-Hydroxyethyl)pyridine 
• 1658-42-0 methyl 2-pyridylacetate 
• 16179-97-8 pyridin-2-yl acetic acid hydrochloride 
• 21883-27-2 methyl (2-pyridin-2-yl)propanoate 

Downstream Products

• 644-98-4 2-isopropylpyridine 
• 194228-34-7 (R)-2-(pyridin-2-yl)propan-1-ol 
• 436145-58-3 2-methyl-2-(pyridin-2-yl)propane-1, 3-diyl-bis(4-methylbenzenesulfonate) 

Relevant academic research and scientific papers

Novel quasi-scorpionate ligand structures based on a bis-N-heterocyclic carbene chelate core: Synthesis, complexation and catalysis

A series of novel quasi-scorpionate CNC donor ligands, MeC(2-C 5H4N){CH2(imidazole-R)} (R = methyl, n-butyl, n-propenyl), in which a chelating bis(NHC) core is supplemented by a hemi-labile pyridyl donor, were prepared. The coordination chemistry of these ligands was investigated with silver, palladium, rhodium and iridium. The single crystal X-ray structures of [Rh(NC2Me)(COD)]Cl 8a and [Ir(NC 2Pr)(COD)]Br 9b were determined. The catalytic potential of the rhodium and iridium complexes was assessed in the transfer hydrogenation of ketones; the iridium complexes, which show superior performance, form very effective and stable catalysts.

Photoenzymatic Hydrogenation of Heteroaromatic Olefins Using ‘Ene’-Reductases with Photoredox Catalysts

Flavin-dependent ‘ene’-reductases (EREDs) are highly selective catalysts for the asymmetric reduction of activated alkenes. This function is, however, limited to enones, enoates, and nitroalkenes using the native hydride transfer mechanism. Here we demonstrate that EREDs can reduce vinyl pyridines when irradiated with visible light in the presence of a photoredox catalyst. Experimental evidence suggests the reaction proceeds via a radical mechanism where the vinyl pyridine is reduced to the corresponding neutral benzylic radical in solution. DFT calculations reveal this radical to be “dynamically stable”, suggesting it is sufficiently long-lived to diffuse into the enzyme active site for stereoselective hydrogen atom transfer. This reduction mechanism is distinct from the native one, highlighting the opportunity to expand the synthetic capabilities of existing enzyme platforms by exploiting new mechanistic models.

CERTAIN PLADIENOLIDE COMPOUNDS AND METHODS OF USE

The present disclosure provides novel pladienolide compounds, pharmaceutical compositions containing such compounds, and methods for using the compounds as therapeutic agents. These compounds may be useful in the treatment of cancers, particularly cancers in which agents that target the spliceosome and mutations therein are known to be useful. Also provided herein are methods of treating cancers by administering at least one compound disclosed herein and at least one additional therapy.

METHODS OF USING SPLICING MODULATORS

This disclosure relates to methods for the treatment of neoplastic disorders by administering Compound 1, or a pharmaceutically acceptably salt thereof, on its own and/or as part of a conjugate or composition, and inducing production of at least one neoantigen.

Iron-Catalyzed β-Alkylation of Alcohols

β-Branched alkylated alcohols have been prepared in good yields using a double-hydrogen autotransfer strategy in the presence of our diaminocyclopentadienone iron tricarbonyl complex Fe1. The alkylation of some 2-arylethanol derivatives was successfully addressed with benzylic alcohols and methanol as alkylating reagents under mild conditions. Deuterium labeling experiments suggested that both alcohols (2-arylethanol and either methanol or benzyl alcohol) served as hydrogen donors in this cascade process.

Iron-Catalyzed Borrowing Hydrogen β- C(sp3)-Methylation of Alcohols

Herein we report the iron-catalyzed β-C(sp3)-methylation of primary alcohols using methanol as a C1 building block. This borrowing hydrogen approach employs a well-defined bench-stable (cyclopentadienone)iron(0) carbonyl complex as precatalyst (5 mol %) and enables a diverse selection of substituted 2-arylethanols to undergo β-C(sp3)-methylation in good isolated yields (24 examples, 65% average yield).

Practical Intermolecular Hydroarylation of Diverse Alkenes via Reductive Heck Coupling

The hydroarylation of alkenes is an attractive approach to construct carbon-carbon (C-C) bonds from abundant and structurally diverse starting materials. Herein we report a palladium-catalyzed reductive Heck hydroarylation of aliphatic and heteroatom-substituted terminal alkenes and select internal alkenes with an array of (hetero)aryl iodides. The reaction is anti-Markovnikov selective with terminal alkenes and tolerates a wide variety of functional groups on both the alkene and (hetero)aryl coupling partners. Additionally, applications of this method to complex molecule diversifications are demonstrated. Mechanistic experiments are consistent with a mechanism in which the key alkylpalladium(II) intermediate is intercepted with formate and undergoes a decarboxylation/C-H reductive elimination cascade to afford the saturated product and turn over the cycle.

C -Methylation of Alcohols, Ketones, and Indoles with Methanol Using Heterogeneous Platinum Catalysts

A versatile, selective, and recyclable heterogeneous catalytic method for the methylation of C-H bonds in alcohols, ketones, and indoles with methanol under oxidant-free conditions using a Pt-loaded carbon (Pt/C) catalyst in the presence of NaOH is reported. This catalytic system is effective for various methylation reactions: (1) the β-methylation of primary alcohols, including aryl, aliphatic, and heterocyclic alcohols, (2) the α-methylation of ketones, and (3) the selective C3-methylation of indoles. The reactions are driven by a borrowing-hydrogen mechanism. The reaction begins with the dehydrogenation of the alcohol(s) to afford aldehydes, which subsequently undergo a condensation reaction with the nucleophile (aldehyde, ketone, or indole), followed by hydrogenation of the condensation product by Pt-H species to yield the desired product. In all of the methylation reactions explored in this study, the Pt/C catalyst exhibits a significantly higher turnover number than other previously reported homogeneous catalytic systems. Moreover, it is demonstrated that the high catalytic activity of Pt can be rationalized in terms of the adsorption energy of hydrogen on the metal surface, as revealed by density functional theory calculations on different metal surfaces.

Enhancement in catalytic proton reduction by an internal base in a diiron pentacarbonyl complex: its synthesis, characterisation, inter-conversion and electrochemical investigation

The reaction of a tripodal ligand (H2L) with a {S2N} donor-set with tri-iron dodecacarbonyl in toluene leads to the isolation of a diiron pentacarbonyl complex 1 as a model for the sub-site of the [FeFe]-hydrogenase. Protonation of this complex under CO (1 atm.) forms quantitatively the hexacarbonyl complex 2H+ with a pendant pyridinium group. Infrared spectroscopic investigations indicate that its pendant pyridinium group dissociates to give hexacarbonyl complex 2 which forms subsequently the pentacarbonyl complex 1. The electrochemistry of these complexes has been investigated. Complex 2H+ exhibits electrocatalysis on proton reduction at a potential more positive by over 200 mV compared to that for other neutral diiron hexacarbonyl complexes. This catalysis is enhanced under a CO atmosphere by freeing the bound base group which acts as a proton relay in the catalysis.

A SOLID STATE FORM OF PLADIENOLIDE PYRIDINE COMPOUNDS AND METHODS OF USE

The present disclosure provides a novel solid state form of pladienolide pyridine compounds, compositions comprising at least one such solid state form, and methods of preparation and use and the same. The novel solid state form of pladienolide pyridine compounds may be useful in the treatment of cancer, such as, for example, cancers in which agents that target the spliceosome and mutations therein are known to be useful.